Sodium borohydride → HCID 86717500, compound

HRID 712048Notes

Reaction equation

HRID 712048 reaction equation
[CH3:1][O:2][C@@H:3]1[CH2:8][C:7](=[O:9])[CH2:6][CH2:5][C@@H:4]1[C:10]([O:12][CH3:13])=[O:11].[BH4-].[Na+]>CO.[NH4+].[Cl-].C(OCC)(=O)C>[OH:9][C@@H:7]1[CH2:6][CH2:5][C@H:4]([C:10]([O:12][CH3:13])=[O:11])[C@H:3]([O:2][CH3:1])[CH2:8]1

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 86717501HCID 86717501, compound

Product 1

HCID 86717500HCID 86717500, compoundYield 92.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of methyl (1S,2R)-2-methoxy-4-oxocyclohexanecarboxylate (racemic, cis-isomer from last step) (1.35 g, 7.25 mmol) in methanol (30 mL) was added sodium tetrahydroborate (270 mg, 7.2 mmol) at −78° C. After stirring for 1 h, the reaction was diluted with sat. NH4Cl solution and ethyl acetate. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, concentrated and purified with flash chromatography (eluting with 70% ethyl acetate in hexanes) to give the desired product (1.26 g, 92%). 1H NMR (500 MHz, CDCl3) δ 3.96 (2H, m), 3.72 (3H, s), 3.38 (3H, s), 2.45 (1H, m), 2.31 (1H, m), 2.11 (1H, m), 1.97 (1H, m), 1.77 (1H, m), 1.50 (2H, m) ppm.

Workup

  1. extractionThe aqueous layer was extracted with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. custompurified with flash chromatography (eluting with 70% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-2b7b6e0c54d94fb895e31c7483656f16
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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